154

Caroline County MD Homes for Sale

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  • /29

    $699,000

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft

    14540 Drapers Mill Rd, Goldsboro, MD 21636

    Searching for your own private oasis with endless possibilities? Welcome to a rare 16.29-acre offering made up of four separate parcels, thoughtfully improved and ready for whatever vision you bring. Whether you dream of a hobby farm, a multi-use homestead, or a private retreat, this property delivers space, versatility, and infrastructure you won’t find anywhere else.Across the acreage

    Amanda Morgan Brenton Realty Group

    14540 Drapers Mill Rd, Goldsboro, MD 21636
  • /72

    $499,990

    $25K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,052 Sq Ft

    22845 Peaviner Rd, Ridgely, MD 21660

    Welcome to your own private retreat! Situated on 4 peaceful acres, this well-maintained 4-bedroom, 2.5-bath home offers the perfect combination of comfort, privacy, and functionality.Inside, you'll find a spacious and inviting floor plan with generous living areas, an updated kitchen, and plenty of room for family and guests. Step outside to the enormous rear deck, an ideal space for

    Chris Rosendale CR Realty

    22845 Peaviner Rd, Ridgely, MD 21660
  • /30

    $259,900

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    325 Carter Ave, Denton, MD 21629

    The joy of one level living!! This home is in Move-in ready condition. Nice size 2 Bedroom 1 Full Bath. Level lot with Patio for enetertaining. Conveniently located within town limits. Shop, parks, restuarants, Brewery.Public Boat ramp to the Choptank River less than a mile.

    Kathleen Brenton Brenton Realty Group

    325 Carter Ave, Denton, MD 21629
  • /2

    $59,900

    • Land
    • 1 Acre
    • $59,900 per Acre

    27286 Willin Ln, Federalsburg, MD 21632

    Private 1-acre wooded lot with deeded access via a dirt road. Enjoy a secluded setting surrounded by nature, perfect for those looking to get away from it all. Great opportunity for a future homesite or recreational use (subject to county approvals). Motivated seller—bring all reasonable offers!

    Janet Todd Harlan C. Williams Co.

    27286 Willin Ln, Federalsburg, MD 21632
  • /20

    $295,000

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    212 Apple Ln, Preston, MD 21655

    Seller is offering a $4,500 credit for new carpet in all 3 bedrooms! Welcome home to this charming 3-bedroom, 2-bath rancher offering the perfect blend of comfort and convenience. Nestled on a quiet street within the city limits, this property provides a peaceful, country-like setting while remaining just minutes from Easton, Denton, Federalsburg, and Cambridge.Step inside to find luxury

    Kayla Walter Keller Williams Realty

    212 Apple Ln, Preston, MD 21655
  • /50

    $450,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,240 Sq Ft

    23118 Tuckahoe Springs Dr, Denton, MD 21629

    Eastern Shore living at its finest! Nestled in the desirable Tuckahoe Springs subdivision, this beautifully maintained home offers the perfect blend of comfort, style, and serene outdoor living.Step inside to an inviting foyer that leads to a dedicated laundry area and an expansive, well‑appointed kitchen featuring cabinetry galore, upgraded stainless‑steel appliances, and quartz

    Amanda Morgan Brenton Realty Group

    23118 Tuckahoe Springs Dr, Denton, MD 21629
  • /28

    $169,000

    • Land
    • 13.8 Acres
    • $12,246 per Acre

    000 Burnt Mill Rd, Ridgely, MD 21660

    This private 13.80 acre hunting tract offers an outstanding opportunity to own a well-managed and affordable recreational property on Maryland's Eastern Shore. Accessed by a deeded right-of-way, the property provides the privacy and seclusion serious hunters appreciate while remaining conveniently located for quick trips to the woods. The tract is comprised of mature hardwood timber and is

    Mike Arajakis Whitetail Properties Real Estate

    000 Burnt Mill Rd, Ridgely, MD 21660
  • /13

    $309,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 1,936 Sq Ft

    245 Briarwood Cir, Denton, MD 21629

    The Upgrades are In! All that's missing is YOU! Beautifully designed new construction interior townhome located in an established community in the heart of Denton, Maryland! Offering 4 spacious bedrooms, 2.5 baths, and an oversized rear-load garage, this home combines modern style with everyday functionality.The open-concept floor plan is perfect for both entertaining and daily living,

    Michelle DiDonato Island Realty, LLC

    245 Briarwood Cir, Denton, MD 21629
  • /58

    $620,000

    • 4 Beds
    • 2.5 Baths
    • 2,704 Sq Ft

    16881 Heritage Hills Ln, Henderson, MD 21640

    Privacy, space, and endless possibilities — this 5.06-acre retreat offers the lifestyle you've been looking for. Tucked into a partially wooded setting at the end of a quiet drive, 16881 Heritage Hills Ln provides the perfect blend of seclusion, functionality, and room to grow. Best of all, there's no HOA, giving you the freedom to truly enjoy your property.Built in 2005, the home offers

    Kaitlyn Collins Benson & Mangold, LLC

    16881 Heritage Hills Ln, Henderson, MD 21640
  • /27

    $315,000

    $15K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,212 Sq Ft

    104 Chambers St, Federalsburg, MD 21632

    Ready to own without the stress? Move in and start your life, not your renovation. This fully renovated home is one your friends will be drooling over. The kitchen steals the show: soft-close navy cabinets with gold hardware and quartz countertops, stainless steel appliances, a deep kitchen sink, stylish floating shelves, and a crisp white tile backsplash. It's the kind of space that makes

    Kaitlyn Collins Benson & Mangold, LLC

    104 Chambers St, Federalsburg, MD 21632
  • /25

    $325,000

    • 4 Beds
    • 2 Baths
    • 1,539 Sq Ft

    306 Sunrise Ave, Ridgely, MD 21660

    Charming & Move-In Ready in Ridgely! This 4-bedroom, 2-full-bath home is priced to sell and ready for its next owner. New $25,000 roof with 50-year transferable warranty! Situated on a spacious corner lot in the friendly town of Ridgely, MD, the property includes 2 utility sheds for extra storage and plenty of parking with off-street spaces in both the front and rear, plus additional on-street

    Vincent De Lorenzo Samson Properties

    306 Sunrise Ave, Ridgely, MD 21660
  • /36

    $370,000

    $20K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 936 Sq Ft

    4455 Smithville Rd, Federalsburg, MD 21632

    This charming ranch-style home, built in 2004, offers a cozy retreat on over 11 acres of serene land, adjoining the picturesque Marshyhope Creek with 3800 acres of Idlewild WMA just across the creek. Inside, discover a traditional floor plan featuring three inviting bedrooms and a country-style kitchen perfect for gatherings. Enjoy the warmth of luxury vinyl plank and carpet flooring throughout.

    Nathan Murray RE/MAX Executive

    4455 Smithville Rd, Federalsburg, MD 21632
  • /31

    $269,000

    • 4 Beds
    • 2 Baths
    • 1,950 Sq Ft

    108 N Academy St, Greensboro, MD 21639

    This charming cape cod home is waiting for your creative touches! Lots of room on three floors. The main floor boasts a large living room with new vinyl flooring. A separate dining room, large kitchen, full bath and mudroom with washer and dryer. The second floor has four spacious bedrooms and a charming vintage bath with claw foot tub! The basement is a perfect place for crafts, hobbies and

    Marcia Rostien Long & Foster Real Estate, Inc.

    108 N Academy St, Greensboro, MD 21639
  • /2

    $21,000

    • Land
    • 6,098 Sq Ft
    • $150,000 per Acre

    12115 Lincoln St, Ridgely, MD 21660

    Vacant lot, check with the county about putting a new house on this lot. There was previously a house on this lot.

    Pamela Geib Long & Foster Real Estate, Inc.

    12115 Lincoln St, Ridgely, MD 21660
  • /2

    $39,950

    • Land
    • 10,454 Sq Ft
    • $166,458 per Acre

    0 Brooklyn Ave, Federalsburg, MD 21632

    Unimproved bulding lot . Did you know that there is a Brooklyn in Federalsburg.

    Barton Johnson/not int Marshy Hope Realty LLC

    0 Brooklyn Ave, Federalsburg, MD 21632
  • /49

    $315,000

    • 4 Beds
    • 2 Baths
    • 2,774 Sq Ft

    111 Maple Ave, Greensboro, MD 21639

    Step into the timeless charm of this beautifully maintained circa-1880 home, where historic elegance meets thoughtful modern updates. Offering over 2,774 square feet of living space, this exceptional residence features 4 spacious bedrooms, 2 full bathrooms, and an abundance of original architectural character that has been lovingly preserved while incorporating today's modern

    Barbara McCaffrey Redfin Corp

    111 Maple Ave, Greensboro, MD 21639
  • /75

    $1,150,000

    • 4,368 Sq Ft

    6354 Statum Rd, Preston, MD 21655

    This wonderful 20 acre property is a horse person’s dream facility. Located in a rural setting, northeast of Preston Maryland. The farm is highlighted by a well-constructed and maintained 75’ x 225’ indoor riding arena, and an 8 stall concrete center aisle horse barn. The barn includes a heated tack room, wash stall with hot water, grooming stall, loft, and overhangs for great ventilation.

    A. John Price Patterson-Schwartz-Middletown

    6354 Statum Rd, Preston, MD 21655
  • /29

    $409,500

    New Construction
    • 4 Beds
    • 2 Baths
    • 1,628 Sq Ft

    5 Sunrise Ave, Ridgely, MD 21660

    Welcome to 5 Sunrise Avenue, a beautifully crafted Lomaxx Custom Homes rancher that’s complete and move in ready! This thoughtfully designed home offers 4 bedrooms, 2 bathrooms, and a spacious 2-car garage, blending modern style with everyday comfort.Inside, you’ll find an open layout featuring luxury vinyl plank flooring, quartz countertops, stainless steel appliances, tile showers, and

    Crystal Smith RE/MAX Executive

    5 Sunrise Ave, Ridgely, MD 21660
  • /2

    $95,000

    • 3 Beds
    • 1.5 Baths
    • 1,408 Sq Ft

    310 E Central Ave, Federalsburg, MD 21632

    Excellent investment opportunity! Over 1/4 acre lot. Home needs TLC. Partial owner financing available. Call for more info. This deal will not last long. Grab it while you have the chance!

    Raphael Szendro R&R Executive Realty

    310 E Central Ave, Federalsburg, MD 21632
  • /47

    $425,000

    • 3 Beds
    • 1.5 Baths
    • 1,356 Sq Ft

    21370 Skeleton Creek Rd, Preston, MD 21655

    Very rustic and private 3 bedroom, 1 and a 1/2 bath log cabin on 15 private wooded acres. There is a large building and a sun porch overlooking a stream running through the property. Excellent hunting property for whitetail deer and turkey!

    Henry Gibbons-Neff Meredith Fine Properties

    21370 Skeleton Creek Rd, Preston, MD 21655
  • /74

    $479,000

    • 3 Beds
    • 3 Baths
    • 2,506 Sq Ft

    104 Charlotte Ave, Federalsburg, MD 21632

    Custom Brick Rancher with 2500 sq ft of living space sitting on over half an acre just outside of downtown Federalsburg overlooking Chambers Park is waiting for you to come see to appreciate. Owners have done many improvements and upgrades to the property, but left some of it's timeless charm. New carpet has been installed on the porch, breakfast nook, and family room July 2026, new windows 2026,

    Shelby Roney Benson & Mangold, LLC

    104 Charlotte Ave, Federalsburg, MD 21632
  • /74

    $599,900

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,938 Sq Ft

    23130 Sparks Rd, Ridgely, MD 21660

    Robert Walker McClain-Williamson Realty, LLC

    23130 Sparks Rd, Ridgely, MD 21660
  • /22

    $467,900

    • 3 Beds
    • 4 Baths
    • 2,713 Sq Ft

    202 N Central Ave, Ridgely, MD 21660

    Charming Victorian home in the heart of Ridgely, ideally situated on a picturesque, tree-shaded corner lot. This timeless property offers classic character, curb appeal, and a prime location close to local amenities. An expansive wraparound front porch sets the stage for this beautiful home, featuring a gracious entryway, stunning columned foyer, and gleaming hardwood floors that enhance its

    Marcia Rostien Long & Foster Real Estate, Inc.

    202 N Central Ave, Ridgely, MD 21660
  • /55

    $340,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft

    306 Caroline Ave, Ridgely, MD 21660

    Charming updated Farmhouse style home with hardwood floors throughout and tiled bathrooms. The open kitchen features quartz countertops, a center island for extra prep space and casual dining, stainless steel appliances, and a tile backsplash. The first floor includes a full bath with a tiled walk-in stall shower, plus a separate laundry/mud room. Dual-zone heating and air for year-round comfort.

    Roger Boyce Chesapeake Real Estate Associates, LLC

    306 Caroline Ave, Ridgely, MD 21660
  • /20

    $299,000

    New Construction $11K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    510 Lincoln St, Denton, MD 21629

    Discover effortless one‑level living in this newly constructed three-bedroom, two-bathroom rancher, completed in 2024 and perfectly positioned in the center of downtown Denton. Modern design, thoughtful upgrades, and an open, airy layout make this home stand out from the moment you step inside.The open-concept living, dining, and kitchen area creates a warm and welcoming flow—ideal for

    Amanda Morgan Brenton Realty Group

    510 Lincoln St, Denton, MD 21629
  • /35

    $250,000

    $15K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,584 Sq Ft

    530 Vaughn Ave, Greensboro, MD 21639

    **Seller is offering $2,500 towards buyers closing costs with a full price offer!** Welcome home to this beautifully updated 3-bedroom, 2.5-bath home built by Gemcraft Homes in 2002. Freshly painted throughout in 2026, this move-in-ready home also features brand-new luxury vinyl plank flooring on the main level and new carpet throughout the second floor, offering a fresh, modern feel from the

    Hunter Geary Hyatt & Company Real Estate, LLC

    530 Vaughn Ave, Greensboro, MD 21639
  • /20

    $205,000

    $5K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 812 Sq Ft

    310 Park Ave, Federalsburg, MD 21632

    This charming farmhouse-style home, built in 1904 has undergone a major renovation in 2026. With 812 square feet of thoughtfully designed living space, this delightful residence features two cozy bedrooms and one and a half bathrooms, making it an ideal retreat for those seeking comfort and style. Step inside to discover a beautifully updated interior adorned with luxury vinyl plank flooring,

    Cheryl Knotts Chesapeake Real Estate Associates, LLC

    310 Park Ave, Federalsburg, MD 21632
  • /59

    $1,250,000

    $250K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,358 Sq Ft

    23071 Tuckahoe Springs Dr, Denton, MD 21629

    New price improvement! Beautifully positioned along the deep protected waters of the Tuckahoe, this exceptional residence has been transformed through an extensive renovation that blends timeless design with comfortable waterfront living. Every improvement was carefully planned, resulting in a home that feels as inviting as it is impressive. The heart of the home is the custom kitchen, where blue

    Sydney Johnson Cohee Sharon Real Estate P.C.

    23071 Tuckahoe Springs Dr, Denton, MD 21629
  • /50

    $469,900

    • 4 Beds
    • 2.5 Baths
    • 2,488 Sq Ft

    9472 Quail Run Rd, Denton, MD 21629

    Denton - 4 bedroom home! This property offers an incredible opportunity to own a home with fantastic features, major mechanical updates, and no HOA! Inside, you will find a traditional layout highlighted by a large country kitchen featuring new countertops and an island. The formal dining room, den (with woodstove) and living room give ample opportunities for flex space. The primary bedroom

    Valerie Brown Coldwell Banker Realty

    9472 Quail Run Rd, Denton, MD 21629
  • /24

    $229,000

    $6K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    122 Julie Ln, Federalsburg, MD 21632

    Welcome to this beautifully maintained newer town home that has been virtually staged was built in late 2025, in the charming Riverwalk community of Federalsburg. Offering 3 bedrooms, 2.5 bathrooms, and modern construction, this home combines today's sought-after finishes with the warmth and small-town charm that make Maryland's Eastern Shore such a desirable place to call home. Close to

    Donna Hollifield Remax Vision

    122 Julie Ln, Federalsburg, MD 21632
  • /39

    $336,900

    Open Sat 10:30AM - 12:30PM $13K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,414 Sq Ft

    504 Main St, Goldsboro, MD 21636

    Welcome to this turn-key, eco-friendly rancher offering single-level living and a modern, open layout. Step inside to a fluid floor plan featuring striking dark wood-look laminate flooring throughout. The spacious living room features a designer green accent wall and flows seamlessly into the country kitchen and dining combination. The kitchen boasts sleek white cabinetry, stainless steel

    Dustin Parker The Parker Group

    504 Main St, Goldsboro, MD 21636
  • /30

    $52,000

    • Land
    • 5.2 Acres
    • $10,000 per Acre

    American Corner Rd, Denton, MD 21629

    5.20 Acres of Wooded Land for Hunting and Recreation on Paved Road in Caroline County, MdCash Price: $52,000Reservation Fee: $900 non-refundable reservation fee secures this property. Reservation fee will be counted toward purchase price or down payment.With your Purchase You Get:1. A Deed in Your Own Name2. 4. NO Closing Fees if you Close Directly In-House with

    Elegment Land Elegment.com

    American Corner Rd, Denton, MD 21629
  • /22

    $389,000

    $20K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,624 Sq Ft

    13790 Drapers Mill Rd, Greensboro, MD 21639

    4 bedroom 2 bath rancher on 3.6 spacious acres on the headwaters of the Choptank.

    Scott Judy Coldwell Banker Waterman Realty

    13790 Drapers Mill Rd, Greensboro, MD 21639
  • /16

    $234,900

    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    163 Riverwalk Terrace, Federalsburg, MD 21632

    This lovely end-unit condo has units on the left side but no units on the right side, offering more quietness and privacy. This beauty has comfort of "home" written all over. Featuring 3 nice-sized bedrooms; a convenient half-bath is located on first level. The kitchen is very well designed with lots of beautiful cabinets and countertops. Bright open floor plan offering ease of flow for the

    Agent Photo

    Bonnie Duley

    Long & Foster Real Estate, Inc.

    163 Riverwalk Terrace, Federalsburg, MD 21632
  • /32

    $599,000

    $26K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,834 Sq Ft

    28402 Liden School Rd, Denton, MD 21629

    This is the one! Approx. 16.77 acres with an owner built 3 bedroom home. One acre with home plus additional acreage. Some acreage is wooded with wild life including, but not limited to, rabbit, deer, and turkey. This home has magnificent kitchen with custom cabinetry and SS appliances, including a 5 burner stove and double wall oven. Pellet stove is included for those cool evenings and damp days.

    Michael Shipley Benson & Mangold, LLC.

    28402 Liden School Rd, Denton, MD 21629
  • /33

    $345,000

    • 4 Beds
    • 2 Baths
    • 2,172 Sq Ft

    612 Market St, Denton, MD 21629

    Step back in time while enjoying the comforts of modern living in this beautifully maintained 1900s historic home nestled in the heart of Denton. Rich with character and timeless charm, this spacious four-bedroom, two-bath residence showcases many of the architectural details that make historic homes so special, including original hardwood floors, detailed moldings, tall ceilings, oversized

    Joelle Dolch Cross Street Realtors LLC

    612 Market St, Denton, MD 21629
  • /73

    $790,000

    $49K PRICE DROP
    • Land
    • 87 Acres
    • $9,080 per Acre

    000 Knife Box Rd, Greensboro, MD 21639

    PRICE IMPROVEMENT!!Located just outside Greensboro in Caroline County, Maryland, this exceptional 87 acre property offers a rare combination of income-producing farmland, diverse wildlife habitat, scenic natural features, and a highly developed hunting setup. The property consists of approximately 50 acres of mature woodland and 37 acres of productive tillable acreage, creating an ideal blend of

    Mike Arajakis Whitetail Properties Real Estate

    000 Knife Box Rd, Greensboro, MD 21639
  • /48

    $385,000

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,040 Sq Ft

    502 Kathryn Ct, Denton, MD 21629

    Updated + Upgraded - Turn-key 4BR/2.5BA contemporary 2-story home on a culdesac lot backing to trees, near historic downtown Denton - a true gem of an Eastern Shore town, perched on the banks of the Choptank River - but tucked away on a residential court. New flooring + paint throughout, new granite counters, new kitchen appliances, new fixtures. Wide open floorplan boasts tall ceilings, spacious

    Charlene Reaser EXP Realty, LLC

    502 Kathryn Ct, Denton, MD 21629
  • /30

    $269,000

    $11K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 864 Sq Ft

    504 Sunset Blvd, Ridgely, MD 21660

    ***Back to Active due to no fault of the Sellers. They have found the home of their choice bring us an offer!! *** This delightful 3-bedroom rancher offers a perfect blend of comfort and community. Built in 1940, this home exudes character with its sturdy block construction and inviting layout. The cozy 864 sq. ft. interior is complemented by essential appliances, including a refrigerator, stove,

    Cheryl Knotts Chesapeake Real Estate Associates, LLC

    504 Sunset Blvd, Ridgely, MD 21660
  • /5

    $900,000

    • Land
    • 26.15 Acres
    • $34,417 per Acre

    1017 Camp Rd, Denton, MD 21629

    Approximately 27.16 acres of development land located within the Town of Denton. The property is currently zoned UR (Urban Residential). Public water and sewer are available in the area; purchasers should independently verify utility capacity, connection requirements, and all development approvals with the Town of Denton and Caroline County. The property is being offered for sale as raw land. A

    Benjamin Alder The Land Group

    1017 Camp Rd, Denton, MD 21629

Showing Results 41 - 80, Page 2 of 4

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